Propiolaldehyde
Chemical compound
From Wikipedia, the free encyclopedia
Propiolaldehyde is an organic compound with molecular formula HC2CHO. It is the simplest chemical compound containing both alkyne and aldehyde functional groups. It is a colorless liquid with explosive properties.[1]
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| Names | |
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| Preferred IUPAC name
Prop-2-ynal | |
| Other names
Propynal; Propiolic aldehyde | |
| Identifiers | |
3D model (JSmol) |
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| 1098318 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.009.871 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C3H2O | |
| Molar mass | 54.048 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.9152 g/cm3 |
| Boiling point | 54–57 °C (129–135 °F; 327–330 K) |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H225, H226, H300, H315, H317, H318, H319, H330, H335 | |
| P210, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions
The compound exhibits reactions expected for an electrophilic alkynyl aldehyde. It is a dienophile and a good Michael acceptor. Grignard reagents add to the carbonyl center.[1] Its explosive properties are attributed to the exothermicity of its polymerization.[1]
Preparation
Occurrence in interstellar medium
Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide-acetylene complex.[3] Another possible pathway is through the reaction of propynylidyne (C3H) with water.[4]